Toward the Synthesis of Pentaheptite Substructure: The Cyclopenta[ef]heptalene to Phenanthrene Rearrangement

IF 9.4 1区 化学 Q1 CHEMISTRY, MULTIDISCIPLINARY
Chang Wang, Chenyu Hu, Weize Wang, Jun Yang, Junzhi Liu
{"title":"Toward the Synthesis of Pentaheptite Substructure: The Cyclopenta[ef]heptalene to Phenanthrene Rearrangement","authors":"Chang Wang, Chenyu Hu, Weize Wang, Jun Yang, Junzhi Liu","doi":"10.31635/ccschem.024.202404765","DOIUrl":null,"url":null,"abstract":"<p>Novel carbon allotropes have long been pursued in synthetic chemistry and materials science, and graphene has been the most well-investigated carbon nanostructure in the past decade. However, an analogous carbon pentaheptite with equal numbers of pentagons and heptagons has not yet been synthesized because designing and synthesizing nonhexagon motifs along two dimensions is challenging. During the synthesis of a pentaheptite substructure (or named nanopentaheptite, <b xmlns:bkstg=\"http://www.atypon.com/backstage-ns\" xmlns:fn=\"http://www.w3.org/2005/xpath-functions\" xmlns:pxje=\"java:com.atypon.frontend.services.impl.PassportXslJavaExtentions\" xmlns:urlutil=\"java:com.atypon.literatum.customization.UrlUtil\" xmlns:xlink=\"http://www.w3.org/1999/xlink\">\n<bold>NPH</bold></b>), which contain four pentagon-heptagon pairs and one heptalene unit, unexpected cyclopenta[<i>ef</i>]heptalene-into-phenanthrene rearrangements were observed for the first time, yielding two novel compounds (<b xmlns:bkstg=\"http://www.atypon.com/backstage-ns\" xmlns:fn=\"http://www.w3.org/2005/xpath-functions\" xmlns:pxje=\"java:com.atypon.frontend.services.impl.PassportXslJavaExtentions\" xmlns:urlutil=\"java:com.atypon.literatum.customization.UrlUtil\" xmlns:xlink=\"http://www.w3.org/1999/xlink\">\n<bold>NPH-R1</bold></b> and <b xmlns:bkstg=\"http://www.atypon.com/backstage-ns\" xmlns:fn=\"http://www.w3.org/2005/xpath-functions\" xmlns:pxje=\"java:com.atypon.frontend.services.impl.PassportXslJavaExtentions\" xmlns:urlutil=\"java:com.atypon.literatum.customization.UrlUtil\" xmlns:xlink=\"http://www.w3.org/1999/xlink\">\n<bold>NPH-R2</bold></b>). Experimental and theoretical results demonstrated that the <b xmlns:bkstg=\"http://www.atypon.com/backstage-ns\" xmlns:fn=\"http://www.w3.org/2005/xpath-functions\" xmlns:pxje=\"java:com.atypon.frontend.services.impl.PassportXslJavaExtentions\" xmlns:urlutil=\"java:com.atypon.literatum.customization.UrlUtil\" xmlns:xlink=\"http://www.w3.org/1999/xlink\">\n<bold>NPH</bold></b> series exhibits narrower energy gaps than that of their hexagonal analog with similar size (e.g., hexa-peri-hexabenzocoronene, <b xmlns:bkstg=\"http://www.atypon.com/backstage-ns\" xmlns:fn=\"http://www.w3.org/2005/xpath-functions\" xmlns:pxje=\"java:com.atypon.frontend.services.impl.PassportXslJavaExtentions\" xmlns:urlutil=\"java:com.atypon.literatum.customization.UrlUtil\" xmlns:xlink=\"http://www.w3.org/1999/xlink\">\n<bold>HBC</bold></b>). Our work reported herein, based on the azulene chemistry, provides new insights into the preparation of novel carbon allotrope pentaheptite nanostructures.</p>","PeriodicalId":9810,"journal":{"name":"CCS Chemistry","volume":"79 1","pages":""},"PeriodicalIF":9.4000,"publicationDate":"2024-10-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"CCS Chemistry","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.31635/ccschem.024.202404765","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0

Abstract

Novel carbon allotropes have long been pursued in synthetic chemistry and materials science, and graphene has been the most well-investigated carbon nanostructure in the past decade. However, an analogous carbon pentaheptite with equal numbers of pentagons and heptagons has not yet been synthesized because designing and synthesizing nonhexagon motifs along two dimensions is challenging. During the synthesis of a pentaheptite substructure (or named nanopentaheptite, NPH), which contain four pentagon-heptagon pairs and one heptalene unit, unexpected cyclopenta[ef]heptalene-into-phenanthrene rearrangements were observed for the first time, yielding two novel compounds ( NPH-R1 and NPH-R2). Experimental and theoretical results demonstrated that the NPH series exhibits narrower energy gaps than that of their hexagonal analog with similar size (e.g., hexa-peri-hexabenzocoronene, HBC). Our work reported herein, based on the azulene chemistry, provides new insights into the preparation of novel carbon allotrope pentaheptite nanostructures.

五庚烯结构的合成:环戊并[ef]庚二烯到菲的重排
长期以来,合成化学和材料科学一直在研究新型碳同素异形体,而石墨烯是过去十年中研究最为深入的碳纳米结构。然而,由于在两个维度上设计和合成非六边形图案具有挑战性,人们尚未合成出具有相同数量五边形和七边形的类似碳五庚烷。在合成含有四对五角庚方和一个庚烯单元的五庚方亚结构(或命名为纳米五庚方,NPH)的过程中,首次观察到了意想不到的环戊并[ef]庚烯-转化为菲的重排,并产生了两种新型化合物(NPH-R1 和 NPH-R2)。实验和理论结果表明,NPH 系列比尺寸相似的六方类似物(如六全六苯并硼烯,HBC)具有更窄的能隙。我们在此报告的工作基于天青石化学,为制备新型碳异构体五庚烯纳米结构提供了新的见解。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
求助全文
约1分钟内获得全文 求助全文
来源期刊
CCS Chemistry
CCS Chemistry Chemistry-General Chemistry
CiteScore
13.60
自引率
13.40%
发文量
475
审稿时长
10 weeks
期刊介绍: CCS Chemistry, the flagship publication of the Chinese Chemical Society, stands as a leading international chemistry journal based in China. With a commitment to global outreach in both contributions and readership, the journal operates on a fully Open Access model, eliminating subscription fees for contributing authors. Issued monthly, all articles are published online promptly upon reaching final publishable form. Additionally, authors have the option to expedite the posting process through Immediate Online Accepted Article posting, making a PDF of their accepted article available online upon journal acceptance.
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
确定
请完成安全验证×
copy
已复制链接
快去分享给好友吧!
我知道了
右上角分享
点击右上角分享
0
联系我们:info@booksci.cn Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。 Copyright © 2023 布克学术 All rights reserved.
京ICP备2023020795号-1
ghs 京公网安备 11010802042870号
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术官方微信